Water → HCID 53685925, compound

HRID 1109021Notes

Reaction equation

HRID 1109021 reaction equation
[O:1]([CH2:8][C:9]#[C:10]/[CH:11]=[CH:12]\[C:13]#[C:14][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O[Li].O>C1COCC1.CCOCC>[O:1]([CH2:8][C:9]#[C:10][CH:11]=[CH:12][C:13]#[CH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86746682HCID 86746682, compound

Product 1

HCID 53685925HCID 53685925, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of step (b) (5.0 g, 19.7 mmol) in 20 mL THF was added 5 mL of water and LiOH-H2O (5.6 g, 133 mmol). The solution was stirred for 4 h, diluted with ether and washed with water. The aqueous layer extracted with ether and then ethyl acetate. The organic fractions were combined, dried (MgSO<) and concentrated. The residue was chromatographed over silica (30:1 hexane/ethyl acetate) to give 3.37 g of (94%) of 7-phenoxy-3-heptene-1,5-diyne.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer extracted with ether
  3. dry with materialdried (MgSO<)
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica (30:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-16f8203c0566432bbe37acd47b90e74c
Source dataset
uspto-grants-1994_06
Patent number
US05318989

Reaction notes

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